Efficient total synthesis of the antitumor agents actinobolin and bactobolin are proposed which both utilize the key bicyclic intermediate lactone. A route to the Lactone has been outlined which involves a stereoselective intramolecular ene-reaction of an electron deficient imine. An alternate strategy to prepare the Lactone has been described which uses an intramolecular nitrone or nitronate [3+2]-cycloaddition to afford the proper ring system and stereochemistry. Steps for the elaboration of the Lactone to actinobolin and bactobolin have been detailed. Syntheses of several C-3 analogs of actinobolin and bactobolin have also been proposed. Analogs and synthetic intermediates will be submitted to NCI for antitumor testing.